기본 정보
- CAS
112828-00-9- 표준 SMILES
C=C1/C(=C\C=C2/CCC[C@]3(C)[C@@H]([C@H](C)/C=C/[C@@H](O)C4CC4)CC[C@@H]23)C[C@@H](O)C[C@@H]1O- InChIKey
LWQQLNNNIPYSNX-UROSTWAQSA-N- 분자식
- C27H40O3
- 평균 분자량
- 412.6 g/mol
- 단동위원소 질량
- 412.29774514
개요
Calcipotriol is a seco-cholestane that is 26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene carrying additional hydroxy substituents at positions 1, 3 and 24. It is used (as its hydrate) in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. It has a role as an antipsoriatic and a drug allergen. It is a triol, a secondary alcohol, a seco-cholestane, a hydroxy seco-steroid and a member of cyclopropanes.
이름 및 식별자
- 우선 이름
- Calcipotriol
- IUPAC
- trans-(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
- 영어명
- Calcipotriene
- 분자식
- C27H40O3
- 분자량
- 412.6
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
112828-00-9、112965-21-6- PubChem CID
- 5288783
- DTXSID
DTXSID0046648- ChEMBL
CHEMBL1200666- ChEBI
CHEBI:50749- UNII
- 143NQ3779B
- EC Number
- 601-218-4、686-849-3
- Nikkaji
- J367.434G
물성
구조 계산 물성
- XLogP
- 4.3
- 극성 표면적
- 60.7 Ų
- 수소 결합 공여자 수
- 3
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 30
- 형식 전하
- 0
- 복잡도
- 743
실험 및 물리화학적 성질
Human Drugs
Breast Feeding; Lactation; Milk, Human; Dermatologic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Dermatological medicines > Medicines affecting skin differentiation and proliferation
물리화학적 성질
- 녹는점
- 166 · 166-168°C
- 끓는 점
- 582 · 582.0±50.0 °C(Predicted)
- 밀도
- 1.12 · 1.12±0.1 g/cm3(Predicted)
- 저장 조건
- -20 °C · Desiccate at -20°C
- 용해도
- 15 mg/mL, · DMSO: 용해성15mg/mL, 투명
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 14.29 · 14.29±0.20(Predicted)
- 색상
- White to off-white
- 안정성
- Light and Temperature Sensitive, Light And Temperature Sensitive
- InChIKey
- LWQQLNNNIPYSNX-HCHVWAPNSA-N
- SMILES
- [C@@H]1(O)C/C(=C/C=C2\CCC[C@@]3(C)[C@@]\2([H])CC[C@@H]3[C@H](C)/C=C/[C@H](C2CC2)O)/C(=C)[C@@H](O)C1
화학적 성질
White Crystalline Solid
안전 및 규제
GHS 분류
GHS Classification
Danger
H300+H310 (16.7%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
P203, P260, P261, P262, P263, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
유해성 정보
Hazard Classes and Categories
Acute Tox. 2 (83.3%)
Acute Tox. 3 (100%)
독성 정보
Exposure Routes
Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.
Toxicity Summary
The precise mechanism of calcipotriol in remitting psoriasis is not well-understood. However, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor, while being less than 1% as active as the calcitriol in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis, and it is thought that the binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation related genes.
안전 데이터
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- 독성
- dog,LD50,skin,> 1500ug/kg (1.5mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)MUSCULOSKELETAL: OTHER CHANGESGASTROINTESTINAL: NAUSEA OR VOMITING,Journal of Toxicological Sciences. Vol. 21(Suppl,
- HS 번호
- 2906195000
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26
- Hazard Classifications
- Acute Tox. 1 DermalAcute Tox. 2 OralEye Irrit. 2Repr. 2Skin Sens. 1BSTOT RE 1
- 스토리지 클래스
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
화학 및 산업
약리 정보
ATC Code
D05AX52
D - Dermatologicals
QD - Dermatologicals
D05AX02
Mechanism of Action
The precise mechanism of calcipotriol in remitting psoriasis is not well-understood, however, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor while being less than 1% the activity in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis and are believed to undergo modulation of gene expression with binding of calcipotriol to the VDR. This modulation is thought to affect gene products related to cell differentiation and proliferation.
Metabolism/Metabolites
Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.
Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound. Route of Elimination: The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.
FDA Pharmacological Classification
143NQ3779B
CALCIPOTRIENE
Chemical Structure [CS] - Vitamin D
Established Pharmacologic Class [EPC] - Vitamin D Analog
Calcipotriene is a Vitamin D Analog.
CALCIPOTRIENE
Absorption, Distribution and Excretion
Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.
The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.
용도 및 제조
Uses
Use (kg) in USA (2002): 4
For the treatment of moderate plaque psoriasis in adults.
응용 분야
개요Calcipotriene also known as Calcipotriol, is a topical vitaminD3 derivative effective in the treatment of psoriasis vulgaris. The drug acts by binding to vitamin D3 receptors in the skin keratinocytes, producing an elevation in cell differentiation and a reduction in cell proliferation. Although its efficacy is comparable to calcitriol, calcipotriol exhibits at least 100 times less effect on calcium metabolism in rats.
용도Calcipotriene is an antipsoriatic that is a vitamin D3 analogue with low calcemic activity. It works by regulating the production and growth of skin cells. In the United States, this drug was first marketed under the trade name Dovonex and is used mainly for the treatment of psoriasis. It is one of the most effective non glucocorticoid topical drugs for the treatment of localized psoriasis.This drug has many off-label applications that are alternative therapies for many dermatologic diseases.
제조 방법
A convergent approach for the total synthesis of calcipotriol (brand name: Dovonex), a proven Vitamin D analog used for the treatment of psoriasis, and medicinally relevant synthetic analogs is described.A Synthesis of calcipotriol via a Key Electroreductive Cross-coupling ApproachCalcipotriol is currently the most successful VitD analog and is prescribed for the treatment of psoriasis, an autoimmune skin disease.
상·하류 제품 정보
상류 원료
하류 제품
공급사100 곳
추가 설명
정의ChEBI: Calcipotriol is a seco-cholestane that is 26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene carrying additional hydroxy substituents at positions 1, 3 and 24. It is used (as its hydrate) in combination with betamethasone dipropionate, a corticosteroid, for the topical treatment of plaque psoriasis in adult patients. It has a role as a drug allergen and an antipsoriatic. It is a member of cyclopropanes, a secondary alcohol, a triol, a hydroxy seco-steroid and a seco-cholestane.
관련 반응
화합물 노트
불러오는 중…